反应详情

温度

90 °C

4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (6.8 g, 22.8 mmol), 5-chloropyridine-3-boronic acid (3.95 g, 25.1 mmol), cesium carbonate (22.3 g, 68.4 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1.67 g, 2.28 mmol) were combined in a vial that had been oven-dried and flushed with nitrogen. Dioxane (73 mL) and water (18 mL) were added, and the vial was sealed and heated to 90° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C19H20Cl2N4 [M+H]+ 375. found 375.

1. customhad been oven-dried
2. customflushed with nitrogen
3. additionDioxane (73 mL) and water (18 mL) were added
4. customthe vial was sealed
5. temperatureThe reaction mixture was cooled to room temperature
6. additiondiluted with ethyl acetate
7. washwashed with water
8. washThe organic layer was washed with brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient)